Hillsmere vacation rentals

We found 31 vacation rentals — enter your dates for availability

Discover a selection of 10 homes and other vacation rentals in Hillsmere that are perfect for your trip. Whether you're going on vacation with family or friends, vacation rentals have the amenities you need and want for your stay, which might include WiFi and a washer and dryer. No matter what you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Hillsmere

Why visit Hillsmere

  • Scenic Hillsmere Shores: Enjoy the picturesque views and relaxing atmosphere of Hillsmere Shores, perfect for unwinding by the water.
  • Outdoor Activities: Take advantage of the local boat ramps and nearby parks for family-friendly outdoor adventures.
  • Historic Charm: Explore the rich history of the area through its historic houses and charming neighborhoods.
  • Variety of Accommodations: Choose from cozy cottages, modern apartments, or private vacation homes to suit your style and budget.
  • Welcoming Community: Experience the friendly vibe of Hillsmere, making it ideal for solo travelers, families, or groups of friends.

Popular types of accommodation around Hillsmere

If you're exploring vacation rentals in Hillsmere, you're in for a treat. Our most popular accommodations include charming Houses, cozy Cottages, and modern Apartments. Whether you're searching for Hillsmere Shores Apartments, studio options, or spacious bedroom apartments, we have a variety of choices to suit your needs. Enjoy your stay with transparency, savings, and the reassurance of finding the perfect getaway in Hillsmere.

  • Houses: The top choice for visitors to Hillsmere, offering spacious and comfortable accommodations perfect for families or groups.
  • Cottages: These quaint and charming retreats are ideal for a cozy getaway, providing a unique and intimate atmosphere.
  • Apartments: A convenient option for travelers, offering modern amenities and a home-like feel in the heart of the community.
  • Condos: Popular among vacationers, condos provide a blend of luxury and comfort, often featuring great views and shared amenities.
  • Cabins: Perfect for nature enthusiasts, cabins offer a rustic escape with a touch of adventure in a serene setting.**

Top attractions in and around Hillsmere

Hillsmere, Annapolis, offers a delightful blend of outdoor, family, and urban experiences. Visitors can explore urban parks, marinas, and historic houses, making it a perfect destination for those seeking culture and outdoor activities. Don't miss the scenic Hillsmere Shores, which adds to the charm of this lovely area. Whether you're traveling solo, with family, or friends, Hillsmere promises a memorable vacation filled with exploration and relaxation.

  • U.S. Naval Academy: A prestigious military institution steeped in history, offering beautiful architecture and scenic views. Visitors can explore the grounds, view historic artifacts, and appreciate the dedication of future naval officers.
  • Maryland Quiet Waters Park: A serene urban park perfect for families, featuring walking trails, picnic areas, and art installations. It's an oasis for outdoor enthusiasts looking to unwind amid nature.
  • Chesapeake Bay Bridge: An engineering marvel, this modern bridge offers breathtaking views of the Chesapeake Bay and connects two vibrant regions, ideal for memorable photographs and scenic drives.

Things to do recommended for couples

For a romantic getaway in Hillsmere, consider a sailing adventure at Annapolis Sailing School, just 2 miles away. Immerse yourselves in culture at the Ballet Theater of Maryland, also 2 miles away, or enjoy a wine tasting at Thanksgiving Farm Wines, located 8 miles away, for a perfect evening.

Things to do recommended for families

Your family will have a blast at the Navy-Marine Corps Memorial Stadium, just 3 miles from Hillsmere, soaking in the sports atmosphere. For some arcade fun, visit Annapolis Bowl, located 4 miles away. Don't miss the relaxation vibes at Allen Pond Park, a short drive of 12 miles.

Things to do recommended for groups

Explore the Annapolis Mall Shopping Center for shopping and entertainment, play a round at South River Golf Links for outdoor fun, or enjoy a captivating performance at The Colonial Players theater, all within a short drive from Hillsmere.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Hillsmere

When you're planning a trip, whether you're traveling with a group, your family, bringing along pets, or seeking extended stays, be sure to prioritize your preferences while filtering your options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Hillsmere with a group: Think about how many bedrooms you'll require and any additional features you might want, like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily refine your search on Vrbo to include all these options and more.
  • Traveling to Hillsmere with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions can make a big difference in your experience.
  • Taking your pets with you to Hillsmere: For many families, a vacation wouldn’t be the same without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and cozy beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Hillsmere: If you're in search of vacation rentals with special offers for stays of a month or more, you've come to the right spot. By utilizing the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include amenities like parking, a well-equipped kitchen, or a private pool in your search for the perfect getaway.

Where to stay near Hillsmere

Hillsmere, Annapolis, offers a delightful mix of family-friendly outdoor activities and a relaxing atmosphere. Explore nearby neighborhoods that boast quiet streets and welcoming communities. Enjoy the scenic Maryland Quiet Waters Park for a peaceful retreat, or take advantage of the local boat ramps for a day on the water. With its rich history and friendly vibe, Hillsmere is an ideal destination for a memorable vacation experience.

  • Annapolis: Nestled on the shores of the Chesapeake Bay, Annapolis is a vibrant city known for its rich history and maritime charm. As the state capital of Maryland, it offers visitors an array of attractions, including the historic U.S. Naval Academy, scenic waterfront parks, and bustling shopping centers. Travelers can enjoy family-friendly activities at the local beaches, explore the picturesque streets lined with 18th-century architecture, or take part in outdoor adventures such as sailing and fishing. With an array of dining options and cultural events, Annapolis promises a delightful city experience.
  • Hillsmere Shores: A tranquil village located just half a mile from Hillsmere, Hillsmere Shores is perfect for outdoor enthusiasts and families seeking scenic beauty. This charming area offers access to a national state park, providing ample opportunities for hiking, picnicking, and wildlife observation. Visitors can enjoy the picturesque beaches and serene lakes, making it an ideal spot for relaxation and recreational activities. The community vibe, along with its proximity to motor racing venues and educational facilities, makes Hillsmere Shores a hidden gem for those looking to unwind and connect with nature.
  • Hunt Meadows: Situated 0.6 miles from Hillsmere, Hunt Meadows is a quaint neighborhood that offers a unique blend of culture and city life. Known for its striking modern bridge and historic monuments, this area showcases a rich tapestry of art and heritage. Visitors can explore local parks and enjoy leisurely strolls along tree-lined streets, soaking in the community's charm. The proximity to Annapolis ensures that you have easy access to a variety of cultural and city-themed activities, making Hunt Meadows a delightful addition to your vacation itinerary.

Best time to go to Hillsmere

If you're planning a trip to Hillsmere, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly SunnyModerately LowSlightly Low
February37.9°F (3.3°C)Light RainMostly SunnyModerately LowSlightly Low
March44.6°F (7.0°C)Light RainMostly SunnyModerately LowSlightly Low
April55.0°F (12.8°C)Light RainMostly SunnyAverageAverage
May64.2°F (17.9°C)Light RainMostly SunnyAverageAverage
June73.0°F (22.8°C)Light RainMostly SunnyModerately HighAverage
July78.4°F (25.8°C)Light RainMostly SunnyModerately HighSlightly High
August76.8°F (24.9°C)Light RainMostly SunnyModerately HighSlightly High
September70.7°F (21.5°C)Light RainMostly SunnyAverageSlightly High
October60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
November48.7°F (9.3°C)Light RainMostly SunnyAverageAverage
December41.5°F (5.3°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is a breeze

Are you hoping to save on your next getaway? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your needs.

Unlock savings with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll earn OneKeyCash on the full booking amount. Being the organizer truly has its advantages. Become a member of our One Key rewards program to unlock exclusive savings and earn OneKeyCash on eligible stays. Sign up today and start reaping the rewards.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides a convenient area for you to initiate new travel plans, refine existing ones, or manage your current reservations. Your saved or booked properties are thoughtfully categorized into Potential, Upcoming, or Current Trips for easy access. To discover the features of Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Hillsmere?
In Hillsmere, vacation houses and cottages are the most popular types of vacation rentals, with several available throughout the area. These properties are typically situated in serene neighborhoods, providing a peaceful retreat for visitors. Most vacation houses feature spacious living areas, fully equipped kitchens, and outdoor spaces, superb for enjoying the pleasant Maryland weather. Cottages tend to offer a charming, cozy atmosphere, often with rustic decor and comfortable furnishings.
Are there any beach house rentals in Hillsmere?
In Hillsmere, Maryland, there are about 15 beach house rentals available, providing a variety of options for travelers. These rentals are typically situated in scenic neighborhoods close to the water, offering easy access to the Chesapeake Bay. Guests can expect amenities such as fully equipped kitchens, spacious living areas, and outdoor decks or patios for enjoying the waterfront views. Many properties also feature multiple bedrooms, making them suitable for families or groups looking to relax and unwind by the beach.
How much does it cost to rent a vacation home in Hillsmere?
Prices for vacation rentals in Hillsmere vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Hillsmere to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Hillsmere vacation house rentals?
You can find great discounts on house rentals in Hillsmere on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Hillsmere?
In Hillsmere, popular vacation rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals with ease. Many properties also feature blenders for smoothies or other beverages, enhancing the kitchen experience. Outdoor spaces are a highlight, with patios available for relaxation and enjoying the pleasant surroundings. Additionally, travelers can expect coffee and tea makers in most rentals, ensuring a warm beverage is always at hand to start the day.
Are there any family house rentals in Hillsmere?
In Hillsmere, Maryland, there are several family-friendly house rentals available. This charming neighborhood is close to the picturesque Chesapeake Bay, offering a superb setting for family getaways. Many of these homes come equipped with spacious living areas, fully stocked kitchens ideal for preparing family meals, and outdoor spaces for children to play or for family barbecues.

Additionally, visitors can enjoy amenities like air conditioning and Wi-Fi for added comfort and convenience. The nearby Broadneck Park features playgrounds, sports fields, and walking trails, making it a great spot for outdoor activities.
Can I rent a vacation home with a pool or hot tub in Hillsmere?
In Hillsmere, Maryland, there are several vacation homes available for rent that feature pools or hot tubs. This charming community near the Chesapeake Bay offers a serene environment for travelers seeking relaxation. Many properties come equipped with private pools, hot tubs, and spacious outdoor areas, superb for enjoying sunny days or unwinding in the evenings. Inside, travelers can expect amenities such as fully equipped kitchens, comfortable living spaces, and access to Wi-Fi, ensuring a pleasant stay.
Are there any Hillsmere vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Hillsmere with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there pet-friendly vacation rentals in Hillsmere?
Yes, you can book pet-friendly vacation rentals in Hillsmere, Maryland. This charming waterfront community offers several options for travelers seeking accommodations that welcome pets. Many of the available rentals are equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups traveling with pets.

Hillsmere is conveniently located near Sandy Point State Park, which features pet-friendly areas and trails for outdoor activities. This park provides ample opportunities for walking and enjoying nature with your furry companions. Additionally, the local area has pet-friendly cafes and shops, enhancing the overall experience for travelers with pets.
Can I find long-stay vacation rentals in Hillsmere?
A long-stay vacation rental in Hillsmere is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Hillsmere for a vacation rental?
The best time to visit Hillsmere for a vacation rental is during the peak season from May to July, with July being particularly popular. This vibrant period attracts families and outdoor enthusiasts who want to enjoy the warm weather and the myriad of activities available in the area. Expect daytime temperatures to range from the mid-70s to low 90s Fahrenheit, creating ideal conditions for outdoor adventures.

During these months, visitors can take advantage of the stunning waterfront, engaging in activities such as kayaking, paddleboarding, or simply relaxing on the beach. The local community often hosts various events and festivals, providing a lively atmosphere that enhances the experience for travelers looking to immerse themselves in the local culture.

If you're aiming for a more budget-friendly option, consider visiting in November. This month offers a quieter, more peaceful ambiance, great for those who enjoy a slower pace while still appreciating the natural beauty of Hillsmere. It's an excellent time for cozy indoor activities or exploring the scenic trails without the summer crowds.

Ultimately, your choice of timing will depend on whether you prefer the bustling excitement of peak summer activities or the tranquil charm of the off-season.
Are there any remote work vacation rentals in Hillsmere?
In Hillsmere, Maryland, there are several vacation rentals that cater to remote workers. This charming community near the Chesapeake Bay offers a peaceful environment, ideal for those looking to balance work and leisure. Many of the available properties come equipped with essential remote work amenities, such as high-speed Wi-Fi, dedicated desk spaces, and ergonomic desk chairs, ensuring a comfortable workspace.

Travelers can enjoy the local scenery during breaks, with nearby parks and waterfront access providing opportunities for relaxation and outdoor activities. The area's proximity to Annapolis also allows for easy access to additional amenities, dining options, and cultural experiences. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Hillsmere vacation rental?
Book your Hillsmere vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Hillsmere?
In Hillsmere, Maryland, visitors can enjoy a variety of attractions that showcase the area's natural beauty and community spirit. One of the key highlights is the Hillsmere Community Park, which features playgrounds, sports fields, and access to the scenic South River, making it superb for outdoor activities and family gatherings. The nearby Sandy Point State Park offers sprawling beaches, hiking trails, and picnic areas, ideal for those looking to enjoy the waterfront and nature.

Additionally, Hillsmere's proximity to Annapolis allows easy access to historical sites like the Maryland State House and the United States Naval Academy, enhancing the cultural experience for travelers.
Can I change or cancel my Hillsmere home rental booking on Vrbo?
To find Hillsmere vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Hillsmere vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More Vacation Ideas